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Ok I looked into it a bit more, and this is what I found out..
my .lg file isn't producing a trade.dat, I don't know why.
Also, I took one of my old files, and did a test run through and had no problems at all. The differences between this league and the old ones are that I just created this, set all teams to computer, and ran the season through. I didn't manage any teams because I wanted to build a little history before I jumped in as the GM. I assume that caused it to not make a trade.dat as well.
Is that a known thing where you need to make GM moves in a season in order for CATO to work? Thanks!
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